My tour

Charming Cape Cod & Nantucket


cape cod black sheep

Rich with coastal New England charm, Cape Cod is at its most beautiful during our summer and autumn visits. You’ll cycle the car-free Cape Cod Rail Trail through coastal villages alongside cranberry bogs, lush marshlands and rolling sand dunes. Off the bike, you’ll stroll the beaches and nature trails, kayak and whale watch. All this and you’ll still have free time to relax and explore.

Road bike
6 days
168 km / 104 mi
$ 3,295.-
  • Lodging in charming Inns
  • Meals included: 4x breakfast, 2 x lunch and 4 x dinner.
  • Ride-friendly snacks and beverages throughout each day
  • Hybrid or alloy road bike rental included– carbon road bike or E-bike available for an upgrade fee
  • Whale watch tour included.
  • Services of professional trip leader(s)
  • Van support during the trip & porterage service
  • Tour operators T-shirt, wool socks, water bottles & luggage tags
  • Deposit for this tour is $750 pp



Road bike
6 days
Easy = untrained, normal physical condition
Moderate = regular cyclist, good condition
Challenging = experienced, well trained
Guided = with cycling guide(s) - support van
Self Guided = individual - directions+maps
Daily distance
60-80 km / 37-50 mi
Total distance
168 km / 104 mi
Deluxe = 4-5 star hotel or excellent B&B
Basic = 1-2 star hotel/motel or B&B
Camping = tent, sports hall or campus
Deluxe, full board
Luggage transport
Daily luggage transfers
01 Jun 2020 - 30 Sep 2020
Private tour, available from 4 participants in one booking. Every year from June 1 - 30 September
Airport at start
Int. airport Boston
Airport at finish
Int. airport Boston


Price per person
The tour price per person
$ 3,295.-
upgrade carbon bike
We carry mostly Cannondales with some Specialized. Out full carbon bikes have either Ultegra or 105
$ 150.-
upgrade hybride E-bike
$ 300.-
Single supplement
If you travel alone a single supplement is charged. With some group tours you can avoid a single supplement by sharing a room with another rider.
$ 995.-


DAY 1: Biking in Chatham

8 miles, Optional Hiking – 1 mile
You’ll start your trip shuttling from Boston to your first night’s lodging in Chatham on Cape Cod. After a brief orientation, you’ll go for a short spin passing Chatham Lighthouse along the way and have the chance to hike on Morris Island. Tonight you’ll enjoy your first dinner together with the group at a local favorite restaurant, just a short walk from our lodging.
Meals included: Dinner

DAY 2: Kayaking Pleasant Bay & Biking to Nickerson

19, 30, or 37 miles
Today you head into Orleans to enjoy a relaxing two-hour kayak on Nauset Marsh before lunch. After your paddle, you’ll head on to Brewster and Nickerson State Park on the blissfully car-free Cape Cod Rail Trail. If you’re looking for more mileage, you can pedal on to the town of Dennis before making your way back to Chatham. Tonight you’ll dine at the Impudent Oyster in downtown Chatham.
Breakfast, Lunch & Dinner

DAY 3: Ferry to Nantucket,

Optional Biking 20 miles
After breakfast you’ll make the 80-minute ferry crossing to the former whaling port of Nantucket. You can learn about the island’s history at the whaling museum as a docent explains the whaling past and Quaker roots of Nantucket. If you’d rather, take a bike ride to Siasconset at the easternmost part of the island, or you can stay in town and visit more historical sights along the cobblestoned streets of the town center. At the end of the day you’ll ferry back to the Cape then shuttle to Chatham, where you’ll enjoy a delicious clambake.
Meals included: Breakfast & Dinner

DAY 4: Biking to Provincetown

17, 39, or 58 miles & Hiking – 2 miles
This morning you bid farewell to Chatham and head down the Cape to Provincetown. You’ll return to the Cape Cod Rail Trail and take it to the end in Wellfleet before spinning along the country roads to the tip of the Cape. Along the way, you’ll be able to stop and tour a lighthouse and hike the surreal White Cedar Swamp Trail. As you travel through Wellfleet and Provincetown, the number of art galleries and unique shops you’ll pass are testimony to the thriving artist community on the Lower Cape.
Meals Included: Breakfast & Lunch

DAY 5: Whale watching cruise

After yesterday, you’ve earned the right to relax a bit. You’ll enjoy a pleasant four-hour cruise on our whale watching vessel out to the plankton-rich feeding grounds where you may see minke, finback or maybe even the majestic white-fluked humpback whales. After your cruise, you’re free to enjoy lunch at the restaurant of your choice and explore, at your own pace, the many shops and sights of Commercial Street in Provincetown. You’ll enjoy a farewell dinner by the water as you recall the week’s events and stories.
Meals included: Breakfast & Dinner

DAY 6: Biking the Province Lands

Biking – 8 miles
After yet another delicious breakfast, you’ll hop on your bike and head toward the very tip of the Cape. You’ll be able to stop at the Cape Cod National Seashore Visitor Center and learn more of the natural history of this coastal region. After our ride, you’ll have the chance to shower & pack up before we shuttle you back to Boston.
Meals included: Breakfast

Map & Routes

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